title: Synthesis of novel bidentate P-chiral diaminophosphine oxide preligands: application to Pd-catalyzed asymmetric allylic substitution reactions.
abstract: We developed a novel (S)-L-phenylalanine derived-bidentate chiral diaminophosphine oxide (DIAPHOX) preligand (S,S(P))-9b, which was successfully applied to Pd-catalyzed asymmetric allylic alkylation and amination. Using the Pd-(S,S(P))-9b catalyst system, asymmetric allylic alkylation and amination proceeded very smoothly, affording the corresponding products in excellent yield with high enantiomeric excess. It is noteworthy that both enantiomers were accessible with high enantiomeric purity using the structurally related DIAPHOX preligands (S,S(P))-9b and a monodentate chiral diaminophosphine oxide preligand (S,R(P))-10a, both of which can be prepared from a single chiral source, (S)-L-phenylalanine.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan.
authors.forename: Teisuke
authors.initials: T
authors.lastname: Harada
authors.forename: Tetsuhiro
authors.initials: T
authors.lastname: Nemoto
authors.forename: Long
authors.initials: L
authors.lastname: Jin
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Hamada
mesh_terms: D000478:Alkylation; D000586:Amination; D002384:Catalysis; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010087:Oxides; D010720:Phosphines; D010165:Palladium